背景:通过涉及乙炔二甲酸二甲酯的一锅三组分反应合成了一系列新型2-(异喹啉-1-基)-螺[羟吲哚-3,3'-吡咯啉],3-苯基咪唑并[5,1-a]异喹啉和N-烷基明胶在氯仿中在〜60°C下持续24小时。
目的:本研究旨在合成新型螺羟吲哚-3,3'-吡咯啉衍生物,并在体外评估其抗炎和自由基清除能力的交叉相关性中的细胞毒性亲和力。
目的:本研究的目的是使用一罐,三组分反应合成一组新型螺羟吲哚-3,3'-吡咯啉衍生物。
方法:通过涉及乙炔二羧酸二甲酯的一锅三组分反应合成了一组新型的螺羟吲哚-3,3'-吡咯啉(8a-i),3-苯基咪唑并[5,1-a]异喹啉和N-烷基异喹啉在氯仿中在〜60°C持续24小时。这些新化合物通过1HNMR表征,13C-NMR,和HRMS光谱数据,并筛选其抗肿瘤,抗炎,抗菌,抗真菌药,和抗氧化活性。
结果:新的合成的螺羟吲哚-3,3'-吡咯啉(8a-i)-测试的化合物显示出显著的抗炎性质并且对PDL成纤维细胞无细胞毒性。然而,它们缺乏抗氧化-DPPH自由基清除能力。值得注意的是,阿霉素和顺铂对各种癌症单层具有抗增殖作用。此外,化合物8b,8d,8f,8h,和8i在结直肠癌和胰腺癌单层中表现出明显的生存力降低特性,以及跨皮肤,肺,前列腺,和宫颈腺癌,在乳腺癌细胞MCF7和T47D中具有较高的细胞毒性。测试的化合物对金黄色葡萄球菌或大肠杆菌都没有显著的抗菌活性。然而,化合物8c,8d,和8f表现出显著的抗真菌特性,表明进一步调查的潜力。
结论:制备了八种新的合成螺[二氢吲哚-3,3-吡咯],characterized,并评估了它们的抗炎和细胞毒性。这些化合物对各种癌症单层显示出显着的抗炎作用和有希望的细胞毒性,尤其是结直肠癌和胰腺癌。一些化合物还表现出抗真菌性质。然而,它们没有表现出显著的抗菌活性。
BACKGROUND: A series of novel 2-(isoquinolin-1-yl)-spiro[oxindole-3,3\'-pyrrolines] were synthesized by a one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 3- phenylimidazo[5,1-a]isoquinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h.
OBJECTIVE: This study aimed at the synthesis of novel spirooxindole-3,3\'-pyrrolines derivatives and in vitro evaluation of cytotoxicity affinities in cross-correlations with their antiinflammation and radical scavenging capacities.
OBJECTIVE: The objective of this study was to use a one-pot, three-component reaction to synthesize a novel set of spirooxindole-3,3\'-pyrrolines derivatives.
METHODS: A novel set of spirooxindole-3,3\'-pyrrolines (8a-i) was synthesized by a one-pot threecomponent reaction involving dimethyl acetylenedicarboxylate, 3-phenylimidazo[5,1-a]isoquinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h. These new compounds were characterized by 1HNMR, 13C-NMR, and HRMS spectral data and screened for their antitumor, anti-inflammatory, antibacterial, antifungal, and antioxidant activities.
RESULTS: The new synthetic spirooxindole-3,3\'-pyrrolines (8a-i)-tested compounds displayed significant anti-inflammatory properties and were noncytotoxic on PDL fibroblasts. However, they lacked antioxidative-DPPH radical scavenging capabilities. Notably, Doxorubicin and cisplatin demonstrated antiproliferative effects on various cancer monolayers. Moreover, compounds 8b, 8d, 8f, 8h, and 8i exhibited pronounced viability reduction properties in colorectal and pancreatic cancer monolayers, as well as across skin, lung, prostate, and cervical adenocarcinomas, with higher cytotoxicity in mammary cancer cells MCF7 and T47D. None of the tested compounds had significant antibacterial activity against S. aureus or E. coli. However, compounds 8c, 8d, and 8f exhibited notable antifungal properties, indicating potential for further investigation.
CONCLUSIONS: Eight new synthetic spiro[indoline-3,3-pyrroles] were prepared, characterized, and evaluated for their anti-inflammatory and cytotoxic properties. The compounds showed significant anti-inflammatory effects and promising cytotoxicity against various cancer monolayers, especially in colorectal and pancreatic cancers. Some compounds also exhibited antifungal properties. However, they did not exhibit significant antibacterial activity.